In May 2025, Donald Trump—having returned to the U.S. presidency—expressed open frustration with both Russian President Vladimir Putin and Ukrainian President Volodymyr Zelenskyy. His anger, conveyed through public statements, social media posts, and leaks from White House aides, was not merely rhetorical. It reflected deeper geopolitical disagreements, failed negotiations, ideological friction, and complex internal and international politics. Understanding Trump’s dual ire requires examining the broader context of the Russia-Ukraine war, America’s strategic interests, and Trump’s characteristic foreign policy style.
1. Russia’s Intensified Drone Warfare and Escalation
One of the most immediate triggers of Trump’s anger at Vladimir Putin was the intensification of Russian drone strikes on Ukrainian cities. In late May 2025, Russia launched a record-breaking 355 drone assaults in a single night, leading to multiple civilian deaths and the destruction of power grids, hospitals, and schools. This was one of the deadliest nights of the war since its inception in 2022.
Trump, who had promised during his 2024 campaign to “end the war in 24 hours,” saw this escalation as a direct challenge to his administration’s credibility. In a post on Truth Social, he wrote, “Putin has gone completely CRAZY—these drone attacks are unacceptable. This is not how peace is made.” His aides echoed that sentiment in press briefings, calling Russia's actions “reckless” and “provocative.”
Behind the scenes, the Trump administration had been trying to pressure Putin into a ceasefire agreement, reportedly offering to lift certain economic sanctions in exchange for a freeze in military operations. The drone strikes, therefore, were seen not just as an act of war but a diplomatic snub that undermined Trump’s authority.
2. Trump-Zelenskyy Oval Office Fallout
Trump’s conflict with Ukrainian President Volodymyr Zelenskyy was more personal and ideological. In February 2025, Zelenskyy visited the White House for high-stakes talks about continued American support. According to multiple reports, the meeting deteriorated rapidly. Trump criticized Ukraine’s delay in organizing elections, calling Zelenskyy a “dictator,” and expressed doubt over how U.S. funds were being spent. He allegedly asked, “How do I know you’re not pocketing the money?”
Zelenskyy pushed back strongly, defending Ukraine’s wartime governance and accusing Trump of trying to coerce Ukraine into political concessions. Their tense exchange was widely reported and signaled a major rift between the two leaders.
Later that month, the Trump administration announced a temporary freeze on military aid to Ukraine pending an “audit” of past expenditures and a reassessment of America’s strategic goals. The move was celebrated by isolationist factions in the GOP but condemned by defense analysts and bipartisan foreign policy experts who feared it would embolden Russia.
3. Disputed Resource-Based Aid Proposal
Adding fuel to the fire was a controversial U.S. proposal requiring Ukraine to commit 50% of its future profits from natural gas, rare earth minerals, and agricultural exports to a U.S.-managed recovery fund in exchange for ongoing military and humanitarian support. This proposal, championed by several of Trump’s economic advisers, was seen by Kyiv as an attempt to economically subjugate Ukraine.
Zelenskyy publicly denounced the proposal, stating, “Ukrainian independence is not for sale.” He argued that while Ukraine needed international assistance, its sovereignty and control over national assets were non-negotiable. The backlash from this proposal not only deepened tensions with Ukraine but also sparked criticism within the European Union, which viewed the deal as predatory.
Trump was reportedly furious at the rejection. He believed the deal was a fair exchange and would help appease American taxpayers concerned about sending “blank checks” to Ukraine. From his perspective, Zelenskyy’s defiance was ungrateful and politically damaging at home.
4. Exclusion of Ukraine from Peace Negotiations
Perhaps the most controversial move by the Trump administration in this context was initiating backchannel peace negotiations with Russia—without Ukraine at the table. These talks, which were later leaked to the press, involved discussions around territorial concessions in Eastern Ukraine, the status of Crimea, and future NATO expansion limits.
Zelenskyy condemned the negotiations, stating that “no deal about Ukraine can happen without Ukraine.” His government warned that any agreement made behind their backs would not be honored and would undermine Ukrainian legitimacy.
European allies, particularly Germany and France, also criticized the exclusionary approach, calling it a “return to Cold War-style power politics.” But Trump defended the strategy, arguing that real progress could only happen between Washington and Moscow, not through “endless committees of diplomats.”
This further infuriated Zelenskyy, who believed Trump was trying to sideline him while legitimizing Russian demands.
5. Growing Domestic and International Backlash
Trump’s increasingly erratic diplomacy began drawing criticism from both sides of the aisle. Prominent Republican senators such as Lindsey Graham and Tom Cotton called for stronger sanctions on Russia and urged the White House to provide more robust support to Ukraine. Meanwhile, Democrats accused Trump of weakening NATO unity and undermining long-standing U.S. alliances.
There was also concern about the mixed signals coming from the administration. While Trump condemned Russian attacks, he simultaneously berated Ukraine’s leadership and withheld aid. These contradictions led to confusion on the global stage and raised questions about whether the U.S. had a coherent foreign policy strategy.
Inside the Pentagon and State Department, morale reportedly dropped, with career diplomats frustrated by constantly shifting directives and the centralization of foreign policy around Trump’s personality and media appearances.
6. Trump’s Unique Diplomatic Style
At the heart of these conflicts lies Trump’s unorthodox diplomatic style. He prides himself on being a dealmaker and often bypasses traditional diplomatic channels in favor of personal negotiations. This approach worked in some cases, such as with North Korea, but has often resulted in confusion and backlash in more complex geopolitical situations like Ukraine.
Trump’s anger at both Putin and Zelenskyy stemmed in part from his belief that both men were undermining his efforts to secure a historic peace deal. He viewed Putin’s escalation as betrayal and Zelenskyy’s resistance as insolence. His frustration, therefore, was as much about optics and control as it was about policy.
In May 2025, Trump was reportedly preparing a high-profile speech outlining his “Peace Through Prosperity” framework, which envisioned post-war reconstruction funded through international investment—but only if Ukraine agreed to terms he saw as practical and mutually beneficial. With both leaders rejecting his overtures, Trump saw his legacy project slipping away, triggering his public outbursts.
Conclusion
Donald Trump’s public anger toward both Vladimir Putin and Volodymyr Zelenskyy in May 2025 was not a coincidence—it was the culmination of multiple failed diplomatic initiatives, ideological conflicts, and clashing personal egos. While Trump’s intentions to end the war were arguably genuine, his methods were controversial and, in many cases, counterproductive.
Russia’s continued military aggression infuriated Trump because it threatened his credibility as a peacemaker. Meanwhile, Ukraine’s refusal to accept economically and politically compromising aid terms angered him because it signaled a lack of deference to his proposed leadership in resolving the war.
Ultimately, Trump’s simultaneous frustration with both sides reflected the impossible position he found himself in—trying to end a complex war quickly through tactics rooted more in business negotiations than statecraft. As the conflict continues, the long-term consequences of these diplomatic breakdowns remain to be seen, both for Ukraine’s future and America’s standing on the world stage.
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